Russian Journal of General Chemistry

, Volume 75, Issue 7, pp 1045–1049 | Cite as

Reaction of (2-Nitro- and 2-Bromo-2-nitroethenyl)phosphonates with 1,3-Cyclohexadiene

  • N. A. Anisimova
  • A. A. Kuzhaeva
  • G. A. Berkova
  • L. I. Deiko
  • V. M. Berestovitskaya


Specific features of the reactions of bis(chloroethyl) 2-nitro- and 2-bromo-2-nitroethenylphosphonates with 1,3-cyclohexadiene were studied. It was found that the reaction with 2-nitroethenylphosphonate occurs stereoselectively and provides bis(2-chloroethyl) endo-(3-nitrobicyclo[2.2.2]oct-5-en-2-yl)phosphonate. 2-Bromo-2-nitroethenylphosphonate under the same conditions gives a mixture of the endo and exo isomers of the corresponding nitrobicyclooctenes. Enhanced tendency of adducts derived from gem-bromonitroethenyl-phosphonates for intramolecular transformations, such as dehydrohalogenation and aromatization, under the cycloaddition conditions was revealed.


Adduct Phosphonate Aromatization Intramolecular Transformation 
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Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • N. A. Anisimova
    • 1
  • A. A. Kuzhaeva
    • 1
  • G. A. Berkova
    • 1
  • L. I. Deiko
    • 1
  • V. M. Berestovitskaya
    • 1
  1. 1.Gertsen Russian State Pedagogical UniversitySt. PetersburgRussia

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